Roll of the Dice
by EmyBlossom93
Summary: Series of 5/1 times one-shots. All Olicity in some way or form. Originally just a one-off but then I decided to add more. ((Story Disclaimer: I do not own Arrow or any related characters.))
1. Ostium

**1.**

While Oliver had learned many lessons over the past five years, one of the most important ones was how important it was to know as much about all the players as possible, whether they be friend or foe. Which was why he now found himself perched outside the window of one Felicity Meghan Smoak.

When he asked Walter earlier if he knew any I.T. experts the girls name had come across Walter's lips quick and easy. Smart and trustworthy was how Walter has described her, a fond look in his eyes. And while Oliver wanted to trust his step-fathers's judgment, he knew he needed to run his own background check on the woman. When nothing suspicious had popped up on the computer, Oliver had used the newly found information to sneak in while he knew she was at work.

Since he had never met the woman in question before, he wasn't sure what to expect from her home. It was nice and tidy, everything organized in such a way that reminded Oliver of the guest bedrooms in his own house. Her bedroom was a little more personalized with pops of color throughout.

If the computer search had barely brought anything up, the search of her apartment had surfaced even less. There was an obvious lack of personal effects in the apartment, only a couple pictures on the computer desk that let him know he was indeed in the correct place.

Probably the most telling part of the place was her closet. Her wardrobe was colorful and full of skirts and dresses, while her shoe collection took the entire space of one wall. Thea would be proud.

But really, Oliver decided, how dangerous could someone be when they wore Panda Flats and Robot Pajamas? Which was why, the next day, he found himself in the IT department, fake smile plastered on as he greeted her, "Felicity Smoak? Hi, I'm Oliver Queen."

**2.**

The night after his world is thrown off-kilter for the nth time, Oliver finds himself once again outside the window to Felicity Smoak's home. Only, this time she's actually inside of it. Sleeping restlessly in her bed, but there none the less. In his hands is the small notebook. The same book that just that afternoon, Felicity had produced its twin. The same book that had been his guiding light since returning from the island. A light that seemed more and more like a moth-trap every day.

He stays there, still as a statue, for a brief while longer before finally making his way through the window (left both unlocked and cracked open and it was honestly a wonder she'd made it this long in this dangerous a city) to complete his late night errand.

Once inside, he steps his way over to her night stand where her glasses lay discarded on top of her tablet. Oliver has snuck past more vigilant and dangerous people than Ms. Smoak, so it's no surprise when she didn't even stir in the slightest. He's learned to embrace the night - stillness, darkness, and stealth.

The glasses are light in his left hand while the small tracker is even lighter in his right. It's a tiny, circular piece no bigger than a screw head and built for the express purpose of tracking others without their knowledge. In this case he'll use it to keep an eye on Felicity. For her own safety, of course.

**3.**

Oliver hasn't slept well since before the island. His nights were spent pacing the floors instead of twisting sheets. And some nights, when it's worse than others and the sky is dark but there are no stars because the city's too contaminated and messy, Oliver suits back up in the green hood as the bow and just goes out. Tonight was one of those nights.

The urban landscape of Starling City is far different from the green forests of the island or the closeness of Hong Kong. And it has dangers of its own as well. Which is something he's learned thoroughly after tonight.

Count Vertigo. With his drugs and bad penny habits. Only this time, Oliver reminds himself, he won't be coming back. Vertigo would be no more. Because he killed him - shot him thrice and sent him flying out a window. Traded one man's life for another's. For her's.

Felicity. Who's window he was currently positioned outside of. It wasn't that much of a shocker. His nightly patrols usually ended up passing her apartment at some point. He needed to make sure she was safe - this night more so than any.

So, he crept around to her bedroom window, intending on only peeking in for a second - long enough to determine that she was safe. Only, she wasn't in her bed or in her room.

Oliver didn't think before sliding her (unlocked) window open and sliding in to her room, silent as the night. He went straight through and into the main hallway where he could hear soft noises.

And there, he found her passed out on the couch - empty tub of mint chip and worn fleece blanket and, most importantly, safe.

**4.**

He knew Diggle was keeping an eye on her and would do anything to keep her safe. If there was one person, other than himself, he could trust to keep Felicity safe, it was John Diggle.

He was also well aware of the fact that going and seeing her himself would do nothing but put her in more danger. Slade Wilson was a smart man who knew how to find his enemies weaknesses. And the more he revealed his connection to Felicity, the closer Slade would be realized just how important the blonde was to him.

But, Oliver had always been a selfish man. And right now what he wanted more than anything was to go to Felicity. To let her smile at him and hold onto him arm like she's the only thing anchoring him down in the storm that had become his life.

So somehow he'd managed to make his way across the rooftops and to her apartment. Her bedroom was dark and empty, but he could hear her and the tv further into the apartment. She was watching an action movie - as if her daily life didn't have enough shoot outs in it.

Oliver slid in through the window, only taking a moment to pick the lock. As quiet as the night, like he'd done multiple times before, he snuck across the bedroom and out into the hallway. He stuck to the shadows and was able to see where she was curled up on the couch, take out in front of her. He had no doubt that she'd ordered enough for herself and John. And probably for leftovers the next day - that girl was forever eating leftovers.

He leaned against the wall and the sudden displacement of weight caused a loud creak to sound. From her apt in the couch, Felicity straightened up and looked over to where he stood.

"Hello?" She asked, eyes scanning. The hallway he stood in was too dark for her to see anything properly.

As she stood up, he slowly made his way back down the hall and out her window - sliding it closed and taking off into the night.

**5.**

Oliver knew Felicity was expecting him so there was really no reason not to use the front door. Except, he hadn't really used it before and old habits tended to die hard. So, it was the window for him once again.

She'd asked once a week for months now but he usually shrugged it off and made some excuse. He didn't quite know what possessed him to accept her invitation of some tv and take out. (Except he totally did know - he was tired of being alone all night. With no place to go but the foundry, he'd become quite the hermit and it wasn't until Roy had made a joke earlier that day that Oliver had even realized it.)

"Something wrong with the front door?" Felicity asked, arms crossed as she stood by her bedroom door in green plaid pajamas.

That was when Oliver realized that almost every time he'd come in through the window, Felicity had been totally unaware of it. This time however, she was very much aware of him sliding in the tiny bedroom window as easily as if he was getting in and out of an Aston Martin.

"Is this how you usually get into a girls home?" She asked, a smile playing on her face, "By sneaking in the window?"

"Only yours."

**6.**

Oliver had spent a lot of time waiting - waiting 5 years to finally come home, waiting for the right moment to strike down an enemy; and, he considered himself pretty good at the act of waiting. At the current moment; however, he didn't think he was particularly patient or good at waiting. Because right now - standing outside of Felicity's front door for the first time while he waited to take her on their second (and hopefully less explosive) date, Oliver wanted nothing more than to just break down the door himself (or sneak in the window as had been his MO the last few times.)

But before he could do either of those things, Felicity was there opening the front door and greeting him with a smile and a babbled hello. She looked stunning in a black cutout dress, hair curled and lips red.

"Nice to see you used the door this time," Felicity said, "I was half worried I should get dressed the bathroom. Less chance of you seeing me naked in there. Not that I walk around naked or anything. Just, you know, I was getting into this dress that totally doesn't allow for a bra. Not that you needed to know that either. And I'm just gonna stop talking now."

"Felicity," Oliver chuckled, "It's fine. I thought the front door might be a more normal place."

"Well, we're not exactly normal, Oliver. I mean, we are doing this all sorts of out of order. We are going on our second date tonight and yet I've already seen you half naked and you've already met my parents and we know more about one another than normal second daters would. And I think I'm just going to invite you in before I babble the night away."

"That would be a good start," Oliver admitted.

"Yeah, a good start," Felicity repeated before holding the door in wider, "Oliver, would you like to come in?"

"I'd love to," Oliver answered and stepped across the entranceway and into the warmth.


	2. Carry Me

_****Five times someo****__****ne had to carry Felicity and the one time Oliver carried her himself.****_

* * *

><p><strong>1 - Nyssa Al Ghul<strong>

Honestly, Felicity hadn't quite known what to expect when Nyssa Al Ghul (heir to the demon) came back into town. Violence? Definitely. Awkard flirting? Probably. Nyssa carrying her like a sack of potatoes? Not really.

Except that's exactly what was happening. They'd gone out together (behind Oliver's back cause he would have vetoed it, they would have argued, she would have won, and Oliver would have channeled his inner grumpy cat the rest of Nyssa's visit) with Felicity tracking down the cellphone signal of a rogue League Assassin. And honestly, everything had been going so well until the assassin had caught sight of Felicity and shot a poisoned dart at her.

Nyssa had taken the man out (Felicity was happy she'd fallen facing away because if the sounds the man made was any indication, she didn't want to see what Nyssa was doing to the traitor) and gone to check on her immediately, "Felicity, try not to move. He hit you with a sedative. It should wear off in a little bit."

Of course, they couldn't really stay there, so Nyssa had taken it upon herself to heave Felicity up onto her shoulder and carry her back to Verdant, where she could wait for the poison to wear off. What they weren't expecting was the rest of the team to be down in the lair.

With a chuckle that took more energy that she would have liked, Felicity was able to ground out, "Heya guys, look, I'm a bag of potatoes."

**2 - Quentin Lance**

Really, Felicity should have known better than to go out drinking. On a good day, she was a lightweight and today was definitely not a good day. No, today was a get-wasted-and-get-laid-and-fuck-the-consequences type of day. And that's exactly what Felicity planned on doing. Or, what she had planned on doing until Detective Quentin Lance walked in the building.

"Ms. Smoak," he greeted her, "How many have you had tonight?"

"Not nearly enough," Felicity answered, trying to turn to see him only to stumble off her stool, "What're you doing here? You can't be here. You're an alcoholic ... recovering alcoholic?"

"I got called about another situation and saw you over here. Thought I'd check up on you," he reached out and steadied her on the stool, "Looks like you've had a few too many. How about I get you home and I'll get our ... mutual friend to find a way to get your car home."

"Don't mention him around me," Felicity protested, but allowed him to help her off the stool, "I'm mad at him. Him and his stupid abs and stupid salmon ladder and dummy face. Thinks he can decide my fate for me. I'm fucking Merida. Without the bow and arrow. That's his thing. Duh."

With that she abruptly fell against him, incoherent ranting still going on under her breath, "I'm afraid I don't feel like walking anymore."

Lance sighed, but picked the girl up anyways, "I am way too old for this."

**3 - Sara Lance**

Felicity had found her life overrun by the male species - from Diggle and Roy in the Foundry to Ray Palmer as her new boss to Oliver trying to be more active in her non-vigilante life everytime Felicity turned in another direction there was a male figure there. And she loved them all, truly (except maybe Ray since she truly knew nothing about him aside from his tenaciousness when it came to getting on her good side … or any side); but, there was only so much testosterone she could take. Every so often she just needed to hang out with other girls.

Unfortunately, her life was lacking in the female variety. Thea was on the outskirts - and out of town; Laurel was in the periphery but slowly making her way in as she became more involved in Team Arrow; Nyssa showed up randomly but that didn't really count since she usually brought some sort of violence; and then she had Sara. Beautiful, badass, well-dressed Sara Lance. Who was currently kneeling on the floor in front of her, painting her toes a vibrant blue and pastel pink.

"You're really good at this," Felicity said, leaning forward to get a better look, "Did you have a lot of practice?"

"Oh yeah," Sara chuckled, flipping her blonde hair over her should and out of the way, "Didn't you know? Nail Polish 101 is the first class I had to take when I enrolled with the League."

"So next time Nyssa's in I should ask her to give me a mani-pedi?" Felicity asked.

She laughed a little harder this time, "Maybe not. Thought it'd be curious to see. I used to do her nails occasionally just like this; well, maybe with less clothes." She patted Felicity's knee and stood up, "Alright, you're all done and it's pretty late. We should probably hit the sack. Hate for you to be tired at work tomorrow."

"I can't walk. My toes are wet and I don't have any of those dividers," Felicity said, setting her empty wine glass on the side table, "Guess you'll just have to carry me."

"You think you're so cute," Sara shook her head, but leaned down and picked her up.

"Well you keep pointing it out," Felicity said, letting out an 'oof' as Sara dropped her on the bed, "Hey! Watch out for the nails!"

**4 - John Diggle**

John had been Felicity's rock since she first joined Team Arrow - and that wasn't just because he had arm muscles the size of small boulders. When she'd first become emerged in the world of bombs and blood and vigilantes she'd freaked and had had a tough time processing everything, despite the multiple tubs of mint choco. It wasn't until John showed up at her house with a couple burgers and a bottle of wine that she began to fully understand everything. John just had a way with words and explaining things.

Of course, at present moment John wasn't really using any words. No, he'd settled for giving Felicity the silent treatment. Which was especially awkward considering he was also holding her. In his arms. Like a child. And how exactly was he carrying her like it was nothing?

"I've carried others heavier than you, Smoaks."

"That was out loud, wasn't it?"

"Isn't that how it usually is?" He asked, smiling despite himself.

"Hey, watch it before I hack your Facebook or something."

"Oh, I'm terrified," John chuckled, "that's scary coming from the girl who twisted her ankle trying to get away from a rat."

She responded by poking his chest, "Hey, rats are creepy. And unsanitary. Yuck."

John just hummed in mock agreement and then, a beat later, "So, are my arms really like small boulders?"

**5 - Roy Harper**

Over the past months of working together officially (as in - with both of them knowing the other was on their side and neither under the influence of any mind altering drugs) Felicity and Roy had developed a strong brother-sister relationship. Which was something that Oliver had noticed, despite how obtuse the team might think him about personal matters. Not that he cared, he was glad the team was getting along so well. But he was jealous of the easy going nature the two shared. Out of all the team they had the least amount of baggage, the least amount of demons. So, if they wanted to share in that easiness and go out to Big Belly together on occasion, he would be the last person to begrudge them that. Which is where they were coming back from now.

The door at the top of the stairs opened and closed with a clang as the two came back in and he heard Felicity reprimanding Roy, "Be careful! Don't drop me!"

Oliver looked up to where they were coming down the stairs, Felicity perched on his back with a shoe in one hand and a Big Belly Burger to-go bag in the other. Beside him, Digg also straightened up and looked over to where their youngest members came down the stairs.

"She okay?" Diggs asked, stepping forward to take the take-out bag from her.

"Yup!" Felicity chuckled, hopping down off Roy's back, "My heel broke getting out of the car and Roy didn't want me walking across the lot in case there was glass or something."

"It's just a good thing your dress wasn't too short today," Roy joked; but, after catching the darkened look on Oliver's face, backtracked, "Not that your dresses are short or anything. You know, I'm just gonna go try and beat up a dummy."

Oliver nodded at him, "You do that, Roy," and turning back to where Felicity sat at the table, "I'll make sure you get home."

"Awwww," Felicity teased over her shoulder, "Are you going to carry me, too?"

**6 - Oliver Queen**

He did carry her.

All the way out to her car. Which she'd been fine with because glass in her foot just didn't seem that appealing to her. Plus, if she wasn't lying to herself, she could admit that it felt pretty good to be in Oliver's arms. Oliver was safety and sturdiness and strength. He was all hard lines and muscles that moved beneath her as she was curled into his chest.

And then he carried her all the way to her apartment. Which, again, was okay because the other day she saw a homeless guy puke in the parking lot and so she didn't want to risk stepping in something ... nasty. Plus, Felicity didn't think she'd turn down a free ride in Oliver's arms.

And then he'd carried her in the building and up the elevator and all the way to her front door. Which she'd protested the entire time. Because what could she possibly step on him her spotless apartment building? But he'd shrugged and mumbled something about making up for the fact that pretty much everyone else had carried her, so, why couldn't he have his turn? Honestly, for a vigilante known for putting the fear of God into people, Oliver could be such a big baby.

And the whole thing was made even more embarrassing by the fact that her next door neighbor, a little old lady named Edith, was in the hallway and saw the entire thing. Which in turn meant her entire building would know by the end of the day tomorrow. She might have to move.


End file.
